反应 #2487474

反应方程式

sodium hydrogen carbonate

6-[2-(butan-2-yl)-6-chloro-5-methoxyindol-1-ylmethyl]pyridine-2-carboxamide

triethylamine

trifluoroacetic anhydride

→

title compound

收率 87.3%

6-[2-(Butan-2-yl)-6-chloro-5-methoxyindol-1-ylmethyl]pyridine-2-carbonitrile

收率 87.3%

溶剂

dichloromethane

反应条件

后处理

1. 1
   温度cooling
2. 2
   萃取followed by extraction with ethyl acetate
3. 3
   洗涤The organic layer was washed with saturated brine
4. 4
   干燥dried over anhydrous sodium sulfate
5. 5
   浓缩concentrated under reduced pressure
6. 6
   其他The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

实验过程

To a solution of 6-[2-(butan-2-yl)-6-chloro-5-methoxyindol-1-ylmethyl]pyridine-2-carboxamide (118 mg) in dichloromethane (1.6 mL) were successively added triethylamine (0.225 mL) and trifluoroacetic anhydride (0.112 mL) under ice-cooling. This mixture was stirred at room temperature for 22 hours. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (98 mg). 1H-NMR (CDCl3) δ ppm: 0.86 (3H, t, J=7.4 Hz), 1.24 (3H, d, J=6.8 Hz), 1.45-1.80 (2H, m), 2.60-2.75 (1H, m), 3.93 (3H, s), 5.40 (2H, s), 6.31 (1H, s), 6.50-6.65 (1H, m), 7.11 (1H, s), 7.14 (1H, s), 7.50-7.70 (2H, m).

来源